CN113387917B - Organic compound containing spirofluorene derivative, organic electroluminescent device and display panel - Google Patents

Organic compound containing spirofluorene derivative, organic electroluminescent device and display panel Download PDF

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CN113387917B
CN113387917B CN202110744372.5A CN202110744372A CN113387917B CN 113387917 B CN113387917 B CN 113387917B CN 202110744372 A CN202110744372 A CN 202110744372A CN 113387917 B CN113387917 B CN 113387917B
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organic compound
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CN113387917A (en
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韩建厅
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Kunshan Govisionox Optoelectronics Co Ltd
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Kunshan Govisionox Optoelectronics Co Ltd
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Abstract

The invention discloses an organic compound containing a spirofluorene derivative, an organic electroluminescent device and a display panel. The structure of the organic compound containing the spirofluorene derivative is shown as a general formula (1). The organic compound takes the spirofluorene derivative as a core, has strong structural rigidity and large steric hindrance, and is not easy to rotate, so that the three-dimensional structure of the organic compound material is more stable. When the organic compound containing the spirofluorene derivative is applied to an organic electroluminescent device, the photoelectric property and the service life of the organic electroluminescent device are effectively improved.

Description

Organic compound containing spirofluorene derivative, organic electroluminescent device and display panel
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic compound containing a spirofluorene derivative, an organic electroluminescent device and a display panel.
Background
Currently, an Organic Light-Emitting Diode (OLED) display technology has been applied in the fields of smartphones, tablet computers and the like, and further will be expanded to the large-size application fields of televisions and the like, however, compared with the actual product application requirements, the performance of the OLED device such as luminous efficiency, service life and the like needs to be further improved. Current research into improving performance of OLED light emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, prolonging the service life of the device, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only is the innovation of the structure and the manufacturing process of the OLED device needed, but also the continuous research and innovation of the OLED photoelectric functional material are needed, and the OLED functional material with higher performance is created.
Disclosure of Invention
In view of the above problems of the prior art, the present invention provides an organic compound containing a spirofluorene derivative, an organic electroluminescent device and a display panel. The photoelectric performance and the service life of the organic electroluminescent device can be effectively improved.
To achieve the purpose, the invention adopts the following technical scheme:
the invention provides an organic compound containing a spirofluorene derivative, which has a structure as shown in a general formula (1):
in the general formula (1), J 1 、J 2 Respectively denoted as C, J 1 And J 2 Through a substituted or unsubstituted vinylidene or ethylene linkage;
the groups of the substituted vinylidene or ethylene are independently selected from cyano, halogen, C 1-10 Alkyl, C 6-30 Aryl, C 2-30 Heteroaryl, one or more of structures shown in a general formula (2) and a general formula (3);
in the general formula (1), A is connected to any carbon atom on benzene rings at two sides of the general formula (1), and A is represented by a structure shown in the general formula (2) or the general formula (3):
in the general formula (2), i is 0 or 1; the X is represented by-O-, -S-, -C (R) 3 )(R 4 ) -or-N (R) 5 )-；
The Z is 1 Each occurrence is identically or differently denoted as N, C or C-R 6 ；
The Ar is as follows 1 Represented by single bonds, substituted or unsubstituted C 6-30 Arylene, substituted or unsubstituted C 2-30 Heteroarylene;
the R is 3 -R 5 Respectively and independently denoted as C 1-10 Alkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 2-30 Heteroaryl;
R 6 represented by hydrogen atom, C 1-10 Alkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 2-30 Heteroaryl;
in the general formula (3), the Z 2 、Z 3 、Z 4 Are each independently represented by N or CH, and Z 2 、Z 3 、Z 4 At least one of which is denoted as N;
the Ar is as follows 2 Represented by single bonds, substituted or unsubstituted C 6-30 Arylene, substituted or unsubstituted C 2-30 Heteroarylene;
the R is 1 、R 2 Respectively and independently expressed as takingSubstituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 2-30 Heteroaryl;
said substitution C 6-30 Aryl, C 2-30 Heteroaryl, C 6-30 Arylene or C 2-30 The heteroarylene group being optionally selected from cyano, halogen, C 1-10 Alkyl, C 6-30 Aryl, C 2-30 One or more of heteroaryl;
the hetero atom in the heteroaryl group and the heteroarylene group is selected from oxygen atom, sulfur atom or nitrogen atom.
Optionally, the C 6-30 Aryl is phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, biphenyl, terphenyl, dimethylfluorenyl or diphenylfluorenyl;
the C is 2-30 Heteroaryl is pyridyl, naphthyridinyl, dibenzofuranyl, dibenzothienyl, carbazolyl or azacarbazolyl;
the C is 1-10 Alkyl is methyl, ethyl, propyl, isopropyl or tert-butyl.
Optionally, the Ar 1 、Ar 2 Each independently represents any one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dimethylfluorenyl group, and a substituted or unsubstituted carbazolyl group.
Optionally, the R 1 、R 2 Each independently is represented by a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl groupAny one of substituted azacarbazolyl.
Optionally, the R 3 -R 5 Each independently represents any one of methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted azacarbazolyl; r is R 6 Represented by any one of a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted azacarbazolyl group.
Optionally, the substituent group is selected from one or more of methyl, ethyl, propyl, isopropyl, tert-butyl, amyl, phenyl, naphthyl, naphthyridinyl, biphenyl, terphenyl, furyl, dibenzofuranyl, carbazolyl or pyridyl.
Alternatively, the organic compound containing a spirofluorene derivative is selected from compounds represented by formula (1) -formula (230).
The invention provides an organic electroluminescent device comprising an anode, a cathode and an organic functional layer, wherein the organic functional layer is positioned between the cathode and the anode, and the organic functional layer contains the organic compound containing the spirofluorene derivative.
Preferably, the organic functional layer includes at least one of a light emitting layer, a hole blocking layer, and an electron transport layer.
The invention provides a display panel comprising the organic electroluminescent device.
The invention has the beneficial effects that:
the compound of the invention takes the spirofluorene derivative as the core, and has strong structural rigidity, large steric hindrance and difficult rotation, so that the three-dimensional structure of the organic compound material of the invention is more stable. Furthermore, after the organic compound containing the spirofluorene derivative is further added with the xanthone or triazine derivative group on the mother nucleus, the glass transition temperature (Tg) of the material is improved, and the stability of the material is improved. The addition of the substituent groups increases the molecular weight of the material, and the evaporation temperature of the organic compound material is low, so that the temperature interval between the processing temperature and the decomposition temperature of the material is widened, and the use processing window of the material is improved.
When the compound is used as a hole blocking layer or an electron transport layer of an OLED, the proper LUMO energy level can effectively realize electron transport, promote the recombination efficiency of excitons in a light-emitting layer, reduce energy loss, and enable the energy of a main body material of the light-emitting layer to be fully transferred to a doping material, thereby improving the light-emitting efficiency of the material after being applied to a device.
When the compound is used as a main material of the luminescent layer, the distribution of electrons and holes in the luminescent layer is more balanced, and the hole injection and transmission performance is improved; the exciton utilization rate and the high fluorescence radiation efficiency are effectively improved, the efficiency roll-off of the device under high current density is reduced, the driving voltage of the device is reduced, and the current efficiency and the service life of the device are improved.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device according to the present invention.
Wherein 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a CPL layer.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the present invention more apparent, the technical solutions in the embodiments of the present invention will be clearly and completely described in the following in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The first aspect of the present invention provides an organic compound containing a spirofluorene derivative having a structure as shown in general formula (1):
in the general formula (1), J 1 、J 2 Respectively denoted as C, J 1 And J 2 Through a substituted or unsubstituted vinylidene or ethylene linkage;
the groups of the substituted vinylidene or ethylene are independently selected from cyano, halogen, C 1-10 Alkyl, C 6-30 Aryl, C 2-30 Heteroaryl, one or more of structures shown in a general formula (2) and a general formula (3);
in the general formula (1), A is connected to any carbon atom on benzene rings at two sides of the general formula (1), and A is represented by a structure shown in the general formula (2) or the general formula (3):
in the general formula (2), i is 0 or 1; the X is represented by-O-, -S-, -C (R) 3 )(R 4 ) -or-N (R) 5 )-；
The Z is 1 Each occurrence is identically or differently denoted as N, C or C-R 6 ；
The Ar is as follows 1 Represented by single bonds, substituted or unsubstituted C 6-30 Arylene, substituted or unsubstituted C 2-30 Heteroarylene;
the R is 3 -R 5 Separately and independently from each otherDenoted as C 1-10 Alkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 2-30 Heteroaryl;
R 6 represented by hydrogen atom, C 1-10 Alkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 2-30 Heteroaryl;
in the general formula (3), the Z 2 、Z 3 、Z 4 Are each independently represented by N or CH, and Z 2 、Z 3 、Z 4 At least one of which is denoted as N;
the Ar is as follows 2 Represented by single bonds, substituted or unsubstituted C 6-30 Arylene, substituted or unsubstituted C 2-30 Heteroarylene;
the R is 1 、R 2 Respectively and independently represented as substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 2-30 Heteroaryl;
said substitution C 6-30 Aryl, C 2-30 Heteroaryl, C 6-30 Arylene or C 2-30 The heteroarylene group being optionally selected from cyano, halogen, C 1-10 Alkyl, C 6-30 Aryl, C 2-30 One or more of heteroaryl;
the hetero atom in the heteroaryl group and the heteroarylene group is selected from oxygen atom, sulfur atom or nitrogen atom.
In an alternative embodiment, C 6-30 Aryl is phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, biphenyl, terphenyl, dimethylfluorenyl or diphenylfluorenyl;
the C is 2-30 Heteroaryl is pyridyl, naphthyridinyl, dibenzofuranyl, dibenzothienyl, carbazolyl or azacarbazolyl;
the C is 1-10 Alkyl is methyl, ethyl, propyl, isopropyl or tert-butyl.
In an alternative embodiment, ar 1 、Ar 2 Each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene groupPhenyl, substituted or unsubstituted terphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted furanylene, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted carbazolylene.
In an alternative embodiment, R 1 、R 2 Each independently represents any one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted azacarbazolyl group.
In an alternative embodiment, R 3 -R 5 Each independently represents any one of methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted azacarbazolyl; r is R 6 Represented by a hydrogen atom, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienylAny one of the azacarbazolyl groups.
In an alternative embodiment, the substituted group is optionally one or more selected from methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, naphthyl, naphthyridinyl, biphenyl, terphenyl, furyl, dibenzofuranyl, carbazolyl or pyridyl.
In an alternative embodiment, in particular, the organic compound containing a spirofluorene derivative is a compound having one of the following structures:
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in a second aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode and an organic functional layer, the organic functional layer being located between the cathode and the anode, the organic functional layer comprising an organic compound comprising a spirofluorene derivative as described in any one of the above.
Preferably, in an alternative embodiment, the organic functional layer includes at least one of a light emitting layer, a hole blocking layer, and an electron transport layer.
A third aspect of the present invention provides a display panel comprising the organic electroluminescent device described above.
The preparation examples and experimental examples of the organic compound containing a spirofluorene derivative according to the present invention will be specifically described below with reference to the accompanying drawings.
Preparation of intermediate F:
the preparation process of the intermediate F1:
under nitrogen atmosphere, 5mmol of raw material A1 and 5mmol of raw material B1 were added to a 250m1 three-necked flask and dissolved in 40ml of tetrahydrofuran, and 15mmol of potassium carbonate and 0.25mmol of Pd (PPh 3 ) 4 The reaction mixture was heated to 65 ℃, refluxed for 18 hours, observed by TLC until the reaction was complete, naturally cooled to room temperature, extracted with diethyl ether, the organic layer was collected, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. The obtained material was purified by a silica gel column (petroleum ether as eluent) to obtain the intermediate C1 of the target product.
A250 ml three-necked flask was prepared, 6.68mol of intermediate C1 was dissolved in 50ml of dimethylformamide, 6.90mol of silver oxide, 0.34mol of palladium acetate and 5.89mol of trifluoroacetic anhydride were added, the reaction mixture was heated to 130℃and refluxed for 36 hours, the reaction was completed, the reaction mixture was naturally cooled to room temperature, quenched by adding water, extracted with ethyl acetate, several layers were collected, dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and the obtained material was purified by a silica gel column (petroleum ether as eluent) to obtain the objective product intermediate D1.
3g of raw material D1 and 30mL of dry tetrahydrofuran are added into a 500mL three-port bottle, the temperature is reduced to minus 78 ℃ under the protection of nitrogen, 4mL of n-hexane solution (2.5 mol/L) of butyl lithium is slowly added dropwise, the reaction is carried out for 30 minutes at minus 78 ℃ after the addition, 2.6g of raw material E1 is slowly added dropwise, the reaction is slowly carried out for two hours after the slow rise to 25 ℃, the stop is carried out, ammonium chloride aqueous solution is added for hydrolysis, the organic layer sodium sulfate is dried and concentrated to dryness, then 20mL of dichloromethane is added for dissolution, 2g of methane sulfonic acid is slowly added into the organic layer dropwise under the nitrogen, the reaction is carried out for 1 hour after the addition to 25 ℃, water is added, the organic layer is concentrated and separated through silica gel column chromatography, petroleum ether is eluted, and the concentrated eluent is obtained to obtain 3.34g of target product F1, and the yield is 75%.
The preparation method of the intermediates F2 to F17 is the same as that of the intermediate F1, and the involved raw materials and reaction equations are as follows:
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preparation of intermediate G:
the preparation process of intermediate G1:
into a 250mL three-necked flask, 10.0mol of raw material F1, 12.0mol of raw material K1 and 0.3g of Pd (dppf) Cl were introduced 2 And 30.0mmol of potassium acetate were added to 100mL of 1, 4-dioxane and reacted at 130℃for 5 hours. The target product is obtained through silica gel column chromatography separation and purification, the HPLC purity is 99.7%, and the yield is 63.8%.
Synthesis of the remaining intermediate G reference the synthesis of intermediate G1.
Synthesis of Compound 1 from preparation example 1
In a 250mL three-necked flask, 11.11mol of intermediate F1 and 7.40mol of intermediate G1 are weighed and dissolved by using a mixed solution of toluene, water and ethanol in a volume ratio of 3:1:1; then 0.012mol Pd (OAc) 2, 7.21mmol Cs are added 2 CO 3 And 14.42mmol Xphos; and carrying out microwave reaction for 3 hours under the condition of nitrogen protection and 120 ℃. After the reaction, an organic layer was extracted with dichloromethane and then dried over anhydrous MgSO 4 Drying, and further separating and purifying by column chromatography to obtain the target product.
Synthesis of Compound 12 from preparation example 2
Synthesis of Compound 30 from preparation example 3
Preparation example 4 Synthesis of Compound 47
Preparation of example 5 Synthesis of Compound 68
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Preparation of Compound 87 Synthesis of example 6
Preparation of Compound 99 of example 7
Preparation of Synthesis of Compound 124 from EXAMPLE 8
Preparation example 9 Synthesis of Compound 133
Preparation example 10 Synthesis of Compound 178
Preparation of example 11 Synthesis of Compound 180
Preparation of example 12 Synthesis of Compound 182
Preparation of example 13 Synthesis of Compound 189
Preparation of Compound 192 of example 14
Preparation example 15 Synthesis of Compound 198
Preparation of example 16 Synthesis of Compound 202
Preparation of Synthesis of Compound 204 from EXAMPLE 17
Preparation of Synthesis of Compound 220 from EXAMPLE 18
The structural characterization of the organic compound containing the spirofluorene derivative obtained in the preparation example is shown in table 1:
TABLE 1
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The organic compound containing the spirofluorene derivative has high glass transition temperature (Tg) and triplet state energy level (T1), and is suitable for HOMO energy level and LUMO energy level, and can be used as a luminescent layer, a hole blocking layer and an electron transport layer material in an organic electroluminescent device. The compounds prepared in the above examples of the present invention were subjected to HOMO level test, LUMO level test, T1 level and thermal performance test, respectively, and the results are shown in table 2.
TABLE 2
Wherein the triplet state energy level T1 is tested by a fluorescent-3 series fluorescence spectrometer of Horiba, and the test condition of the material is 2 x 10 -5 A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, german fast Co., DSC204F1 differential scanning calorimeter) at a heating rate of 10 ℃/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy measurement system (IPS-3), tested as an atmospheric environment; eg was tested by a two-beam uv-vis spectrophotometer (model: TU-1901), lumo=homo+eg. * The illustrated structure corresponds to the following.
As can be seen from the above table data, the organic compound containing a spirofluorene derivative of the present invention has appropriate HOMO energy level, LUMO energy level, and is suitable as a material for a light-emitting layer, a hole-blocking layer, or an electron-transporting layer; meanwhile, the organic compound containing the spirofluorene derivative has higher thermal stability, so that the service life of an OLED device adopting the organic compound is prolonged.
The effect of the organic compound containing a spirofluorene derivative of the present invention applied as a host light-emitting layer or an electron transport layer or a hole blocking layer in a device is described in detail below with reference to device examples 1 to 36 and device comparative example 1. Compared with the device example 1, the device examples 2-12 and the device comparative example 1 have the same manufacturing process, and adopt the same substrate material and electrode material, the film thickness of the electrode material is kept consistent, except that the material of the luminescent layer main body in the device is changed; device examples 13-24 transformed the hole blocking layer material of the device; device examples 25-36 the electron transport layer materials of the devices were varied and the results of the performance tests of the devices obtained in each example are shown in table 4.
Device example 1
As shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, and the anode layer 2 (ITO (15 nm)/Ag (150 nm)/ITO (15 nm)) is washed, that is, sequentially washed with a cleaning agent (SemiClean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, the film thickness was 10nm, and the mass ratio of HT-1 and P-1 was 97:3. Next, HT-1 was evaporated as a hole transport layer 4, with a thickness of 130nm. EB-1 was then evaporated as an electron blocking layer 5, 40nm thick. After the evaporation of the electron blocking layer material is finished, a luminescent layer 6 of the OLED luminescent device is manufactured, the structure of the luminescent layer comprises a compound 1 and GH-2 used by the OLED luminescent layer 6 as main materials, GD-1 as a doping material, the doping proportion of the doping material is 6% (mass ratio), and the thickness of the luminescent layer is 40nm. After the light-emitting layer 6 was deposited, vacuum deposition of HB-1 was continued to give a film thickness of 5nm, and this layer was a hole blocking layer 7. After the hole blocking layer 7, vacuum evaporation of ET-1 and Liq is continued, the mass ratio of ET-1 to Liq is 1:1, the film thickness is 35nm, and the electron transport layer 8 is formed. On the electron transport layer 8, a LiF layer having a film thickness of 1nm, which is an electron injection layer 9, was formed by a vacuum vapor deposition apparatus. An Mg/Ag electrode layer with a film thickness of 15nm was formed on the electron injection layer 9 by a vacuum deposition apparatus, and the mass ratio of Mg to Ag was 1:9, and this layer was used as the cathode layer 10. On the cathode layer 10, a CPL layer 11 was formed by vacuum deposition of CP-1, and the thickness was 70nm.
The molecular structural formula of the related material is shown as follows:
after completing the OLED light emitting device as described above, the anode and cathode were connected by a well-known driving circuit, and the voltage, current efficiency, light emission spectrum, and life of the device were measured. Examples of devices prepared in the same manner and comparative examples are shown in table 3; the test results of the voltage, current efficiency, color and LT95 lifetime at 10000nits luminance of the obtained device are shown in table 4.
TABLE 3 Table 3
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TABLE 4 Table 4
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Wherein the voltage, current efficiency and color coordinates are at a current density of 10mA/cm 2 Tested under conditions, an IVL (current-voltage-brightness) test system (fexostat scientific instruments, su); the life test system is an EAS-62C OLED device life tester of Japanese system technical research company; LT95 refers to the time taken for the device brightness to decay to 95% at 10000 nits.
The results in table 4 show that the organic compound containing the spirofluorene derivative of the present invention can be applied to OLED light-emitting devices as a host material for light-emitting layers, an electron transport layer material, and a hole blocking layer material. Device examples 1-36 achieved a large improvement in both efficiency and lifetime, and in particular a large increase in the device drive lifetime, over comparative example 1.
While the invention has been disclosed by way of examples and preferred embodiments, it is to be understood that the invention is not limited to the disclosed embodiments. On the contrary, it is intended to cover various modifications and similar arrangements as will be apparent to those skilled in the art. The scope of the appended claims is, therefore, to be accorded the broadest interpretation so as to encompass all such modifications and similar arrangements.

Claims (8)

1. An organic compound containing a spirofluorene derivative, characterized by having a structure represented by general formula (1):
in the general formula (1), J 1 、J 2 Respectively denoted as C, J 1 And J 2 Through a substituted or unsubstituted vinylidene or ethylene linkage;
the groups of the substituted vinylidene or ethylene are independently selected from cyano, halogen, C 1-10 Alkyl, C 6-30 Aryl, C 2-30 Heteroaryl, one or more of structures shown in a general formula (2) and a general formula (3);
in the general formula (1), A is connected to any carbon atom on benzene rings at two sides of the general formula (1), and A is represented by a structure shown in the general formula (2) or the general formula (3):
in the general formula (2), i is 0 or 1; the X is represented by-O-, -S-, -C (R) 3 )(R 4 ) -or-N (R) 5 )-；
The Z is 1 Each occurrence is identically or differently denoted as N, C or C-R 6 ；
The Ar is as follows 1 Represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstitutedAny one of naphthylene, substituted or unsubstituted pyridylene;
the R is 3 -R 5 Respectively and independently denoted as C 1-10 Alkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 2-30 Heteroaryl;
R 6 represented by hydrogen atom, C 1-10 Alkyl, substituted or unsubstituted C 6-30 Aryl, substituted or unsubstituted C 2-30 Heteroaryl;
in the general formula (3), the Z 2 、Z 3 、Z 4 Are each independently represented by N or CH, and Z 2 、Z 3 、Z 4 At least one of which is denoted as N;
the Ar is as follows 2 Represents any one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted pyridylene group;
the R is 1 、R 2 Each independently represents any one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group;
said substitution C 6-30 Aryl, C 2-30 The heteroaryl group being selected from cyano, halogen, C 1-10 Alkyl, C 6-30 Aryl, C 2-30 One or more of heteroaryl;
the hetero atom in the heteroaryl group is any selected from an oxygen atom, a sulfur atom or a nitrogen atom.
2. The organic compound according to claim 1, wherein said C 6-30 Aryl is phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, biphenyl, terphenyl, dimethylfluorenyl or diphenylfluorenyl;
the C is 2-30 Heteroaryl is pyridyl, naphthyridinyl, dibenzofuranyl, dibenzothienyl, carbazolyl or azacarbazolyl；
The C is 1-10 Alkyl is methyl, ethyl, propyl, isopropyl or tert-butyl.
3. The organic compound according to claim 1, wherein R 3 -R 5 Each independently represents any one of methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted azacarbazolyl; r is R 6 Represented by any one of a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted azacarbazolyl group.
4. An organic compound according to any one of claims 1 to 3, wherein the substituent groups are optionally selected from one or more of methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, naphthyl, naphthyridinyl, biphenyl, terphenyl, furyl, dibenzofuranyl, carbazolyl or pyridyl.
5. An organic compound containing a spirofluorene derivative, characterized in that the organic compound containing a spirofluorene derivative is a compound having one of the following structures:
6. an organic electroluminescent device comprising an anode, a cathode and an organic functional layer, the organic functional layer being located between the cathode and the anode, characterized in that the organic functional layer contains the organic compound containing a spirofluorene derivative as claimed in any one of claims 1 to 5.
7. The organic electroluminescent device according to claim 6, wherein the organic functional layer comprises at least one of a light emitting layer, a hole blocking layer, and an electron transport layer.
8. A display panel comprising the organic electroluminescent device as claimed in claim 6 or 7.
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CN110964021A (en) * 2018-09-30 2020-04-07 江苏三月光电科技有限公司 Compound with fluorene as core, preparation method and application thereof
CN112479901A (en) * 2019-09-11 2021-03-12 江苏三月光电科技有限公司 Organic compound with indeno-anthracene derivative as core and application thereof
CN112479904A (en) * 2019-09-11 2021-03-12 江苏三月光电科技有限公司 Organic compound with indeno-anthracene derivative as core and application thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110964021A (en) * 2018-09-30 2020-04-07 江苏三月光电科技有限公司 Compound with fluorene as core, preparation method and application thereof
CN112479901A (en) * 2019-09-11 2021-03-12 江苏三月光电科技有限公司 Organic compound with indeno-anthracene derivative as core and application thereof
CN112479904A (en) * 2019-09-11 2021-03-12 江苏三月光电科技有限公司 Organic compound with indeno-anthracene derivative as core and application thereof

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